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Showing NP-Card for Sulforaphane (NP0000226)

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Record Information
Version1.0
Created at2007-01-22 21:33:44 UTC
Updated at2021-08-19 23:57:57 UTC
NP-MRD IDNP0000226
Secondary Accession NumbersNone
Natural Product Identification
Common NameSulforaphane
DescriptionSulforaphane (SFN) is the most characterized isothiocyanate. SFN has received a great deal of attention because of its ability to simultaneously modulate multiple cellular targets involved in cancer development, including: (I) DNA protection by modulating carcinogen-metabolizing enzymes and blocking the action of mutagens; (ii) inhibition of cell proliferation and induction of apoptosis, thereby retarding or eliminating clonal expansion of initiated, transformed, and/or neoplastic cells; (iii) inhibition of neoangiogenesis, progression of benign tumors to malignant tumors, and metastasis formation. SFN is therefore able to prevent, delay, or reverse preneoplastic lesions, as well as to act on cancer cells as a therapeutic agent. Taking into account this evidence and its favorable toxicological profile, SFN can be viewed as a conceptually promising agent in cancer prevention and/or therapy. SFN is the hydrolysis product of glucoraphanin, particularly high in the young sprouts of broccoli and cauliflower. SFN can also be obtained by eating cruciferous vegetables such as brussel sprouts, broccoli, cauliflower, bok choy, kale, collards, arugula, broccoli sprouts, chinese broccoli, broccoli raab, kohlrabi, mustard, turnip, radish, watercress and cabbage (PMID:17134937 ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000226 (Sulforaphane)


  Mrv1652305271900292D          

 10  9  0  0  0  0            999 V2000
    9.7991   -9.0820    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.5136   -8.6695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2280   -8.2570    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9425   -8.6695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6570   -8.2570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3714   -8.6695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0859   -8.2570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8004   -8.6695    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.5149   -8.2570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8004   -9.4945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  2  2  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  2  0  0  0  0
 10  8  1  0  0  0  0
M  END
Download

3D MOL for NP0000226 (Sulforaphane)

HMDB0005792
     RDKit          3D
Sulforaphane
 21 20  0  0  0  0  0  0  0  0999 V2000
   -3.5517    0.7832    0.3814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4261   -0.5850    0.6229 S   0  0  0  0  0  4  0  0  0  0  0  0
   -3.0127   -1.8020   -0.1090 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8413   -0.1489   -0.1227 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1148   -1.2853    0.0706 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4804   -1.0321   -0.5221 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0657    0.1726    0.1313 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3948    0.4935   -0.3759 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8591    1.6330   -0.0439 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5998    3.0695   -0.2629 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4488    1.1664   -0.6675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6029    0.4714    0.5882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2478    1.5890    1.0797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4899    0.7686    0.3965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9350    0.1118   -1.1885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3022   -2.2441   -0.2769 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2848   -1.3707    1.1854 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3928   -0.9254   -1.6207 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0836   -1.9380   -0.3419 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1445    0.0083    1.2120 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4383    1.0641   -0.1358 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  2  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  4 14  1  0
  4 15  1  0
  5 16  1  0
  5 17  1  0
  6 18  1  0
  6 19  1  0
  7 20  1  0
  7 21  1  0
M  END
Download

3D SDF for NP0000226 (Sulforaphane)


  Mrv1652305271900292D          

 10  9  0  0  0  0            999 V2000
    9.7991   -9.0820    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.5136   -8.6695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2280   -8.2570    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9425   -8.6695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6570   -8.2570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3714   -8.6695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0859   -8.2570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8004   -8.6695    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.5149   -8.2570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8004   -9.4945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  2  2  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  2  0  0  0  0
 10  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000226

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CS(=O)CCCCN=C=S

> <INCHI_IDENTIFIER>
InChI=1S/C6H11NOS2/c1-10(8)5-3-2-4-7-6-9/h2-5H2,1H3

> <INCHI_KEY>
SUVMJBTUFCVSAD-UHFFFAOYSA-N

> <FORMULA>
C6H11NOS2

> <MOLECULAR_WEIGHT>
177.288

> <EXACT_MASS>
177.028205359

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
19.108731790879084

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-isothiocyanato-4-methanesulfinylbutane

> <ALOGPS_LOGP>
1.24

> <JCHEM_LOGP>
0.21977109100000025

> <ALOGPS_LOGS>
-1.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6321878230660762

> <JCHEM_POLAR_SURFACE_AREA>
29.43

> <JCHEM_REFRACTIVITY>
49.567699999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.55e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sulforaphane

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0000226 (Sulforaphane)

HMDB0005792
     RDKit          3D
Sulforaphane
 21 20  0  0  0  0  0  0  0  0999 V2000
   -3.5517    0.7832    0.3814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4261   -0.5850    0.6229 S   0  0  0  0  0  4  0  0  0  0  0  0
   -3.0127   -1.8020   -0.1090 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8413   -0.1489   -0.1227 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1148   -1.2853    0.0706 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4804   -1.0321   -0.5221 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0657    0.1726    0.1313 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3948    0.4935   -0.3759 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8591    1.6330   -0.0439 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5998    3.0695   -0.2629 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4488    1.1664   -0.6675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6029    0.4714    0.5882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2478    1.5890    1.0797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4899    0.7686    0.3965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9350    0.1118   -1.1885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3022   -2.2441   -0.2769 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2848   -1.3707    1.1854 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3928   -0.9254   -1.6207 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0836   -1.9380   -0.3419 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1445    0.0083    1.2120 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4383    1.0641   -0.1358 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  2  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  4 14  1  0
  4 15  1  0
  5 16  1  0
  5 17  1  0
  6 18  1  0
  6 19  1  0
  7 20  1  0
  7 21  1  0
M  END
Download

PDB for NP0000226 (Sulforaphane)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  S   UNK     0      18.292 -16.953   0.000  0.00  0.00           S+0
HETATM    2  C   UNK     0      19.625 -16.183   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      20.959 -15.413   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      22.293 -16.183   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      23.626 -15.413   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      24.960 -16.183   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      26.294 -15.413   0.000  0.00  0.00           C+0
HETATM    8  S   UNK     0      27.627 -16.183   0.000  0.00  0.00           S+0
HETATM    9  O   UNK     0      28.961 -15.413   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      27.627 -17.723   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END
Download

3D PDB for NP0000226 (Sulforaphane)

COMPND    HMDB0005792
HETATM    1  C1  UNL     1      -3.552   0.783   0.381  1.00  0.00           C  
HETATM    2  S1  UNL     1      -2.426  -0.585   0.623  1.00  0.00           S  
HETATM    3  O1  UNL     1      -3.013  -1.802  -0.109  1.00  0.00           O  
HETATM    4  C2  UNL     1      -0.841  -0.149  -0.123  1.00  0.00           C  
HETATM    5  C3  UNL     1       0.115  -1.285   0.071  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.480  -1.032  -0.522  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.066   0.173   0.131  1.00  0.00           C  
HETATM    8  N1  UNL     1       3.395   0.493  -0.376  1.00  0.00           N  
HETATM    9  C6  UNL     1       3.859   1.633  -0.044  1.00  0.00           C  
HETATM   10  S2  UNL     1       4.600   3.070  -0.263  1.00  0.00           S  
HETATM   11  H1  UNL     1      -3.449   1.166  -0.668  1.00  0.00           H  
HETATM   12  H2  UNL     1      -4.603   0.471   0.588  1.00  0.00           H  
HETATM   13  H3  UNL     1      -3.248   1.589   1.080  1.00  0.00           H  
HETATM   14  H4  UNL     1      -0.490   0.769   0.396  1.00  0.00           H  
HETATM   15  H5  UNL     1      -0.935   0.112  -1.189  1.00  0.00           H  
HETATM   16  H6  UNL     1      -0.302  -2.244  -0.277  1.00  0.00           H  
HETATM   17  H7  UNL     1       0.285  -1.371   1.185  1.00  0.00           H  
HETATM   18  H8  UNL     1       1.393  -0.925  -1.621  1.00  0.00           H  
HETATM   19  H9  UNL     1       2.084  -1.938  -0.342  1.00  0.00           H  
HETATM   20  H10 UNL     1       2.144   0.008   1.212  1.00  0.00           H  
HETATM   21  H11 UNL     1       1.438   1.064  -0.136  1.00  0.00           H  
CONECT    1    2   11   12   13
CONECT    2    3    3    4
CONECT    4    5   14   15
CONECT    5    6   16   17
CONECT    6    7   18   19
CONECT    7    8   20   21
CONECT    8    9    9
CONECT    9   10   10
END
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SMILES for NP0000226 (Sulforaphane)

CS(=O)CCCCN=C=S
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INCHI for NP0000226 (Sulforaphane)

InChI=1S/C6H11NOS2/c1-10(8)5-3-2-4-7-6-9/h2-5H2,1H3
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View in JSmol
Synonyms
ValueSource
SulforafanChEBI
SulphorafanGenerator
SulphoraphaneGenerator
(R)-SulphoraphaneHMDB
1-Isothiocyanato-4-methylsulphinylbutaneHMDB
MethylsulfoxybutylisothiocyanateHMDB
4-Methylsulphinylbutyl glucosinolateHMDB
(R)-SulforaphaneMeSH
(S)-SulforaphaneMeSH
(+-)-SulforaphaneMeSH
4-MethylsulfoxybutylisothiocyanateMeSH
Chemical FormulaC6H11NOS2
Average Mass177.2880 Da
Monoisotopic Mass177.02821 Da
IUPAC Name1-isothiocyanato-4-methanesulfinylbutane
Traditional Namesulforaphane
CAS Registry Number4478-93-7
SMILES
CS(=O)CCCCN=C=S
InChI Identifier
InChI=1S/C6H11NOS2/c1-10(8)5-3-2-4-7-6-9/h2-5H2,1H3
InChI KeySUVMJBTUFCVSAD-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, CDCl3, simulated)Varshavi.d262021-08-31View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)Varshavi.d262021-08-31View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, CDCl3, simulated)Varshavi.d262021-07-29View Spectrum
Species
Species of Origin
Species NameSourceReference
Arabidopsis thalianaLOTUS Database
Brassica oleraceaKNApSAcK Database
Brassica oleracea var. capitataFooDB
Brassica oleracea var. gemmiferaFooDB
Brassica oleracea var. italicaFooDB
Cardaria drabaKNApSAcK Database
Lepidium drabaKNApSAcK Database
Raphanus sativusKNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sulfoxides. Sulfoxides are compounds containing a sulfoxide functional group, with the structure RS(=O)R' (R,R' not H).
KingdomOrganic compounds
Super ClassOrganosulfur compounds
ClassSulfoxides
Sub ClassNot Available
Direct ParentSulfoxides
Alternative Parents
Substituents
  • Sulfoxide
  • Isothiocyanate
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Sulfinyl compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point368.00 to 369.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility13820 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP0.407 (est)The Good Scents Company Information System
Predicted Properties
PropertyValueSource
Water Solubility2.55 g/LALOGPS
logP1.24ALOGPS
logP0.22ChemAxon
logS-1.8ALOGPS
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area29.43 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity49.57 m³·mol⁻¹ChemAxon
Polarizability19.11 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0005792
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012608
KNApSAcK IDC00050239
Chemspider ID5157
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSulforaphane
METLIN IDNot Available
PubChem Compound5350
PDB IDNot Available
ChEBI ID47807
Good Scents IDrw1120281
References
General References
  1. Fimognari C, Hrelia P: Sulforaphane as a promising molecule for fighting cancer. Mutat Res. 2007 May-Jun;635(2-3):90-104. Epub 2006 Nov 28. [PubMed:17134937 ]
  2. Perocco P, Bronzetti G, Canistro D, Valgimigli L, Sapone A, Affatato A, Pedulli GF, Pozzetti L, Broccoli M, Iori R, Barillari J, Sblendorio V, Legator MS, Paolini M, Abdel-Rahman SZ: Glucoraphanin, the bioprecursor of the widely extolled chemopreventive agent sulforaphane found in broccoli, induces phase-I xenobiotic metabolizing enzymes and increases free radical generation in rat liver. Mutat Res. 2006 Mar 20;595(1-2):125-36. doi: 10.1016/j.mrfmmm.2005.11.007. [PubMed:16442570 ]
  3. Jo EH, Kim SH, Ahn NS, Park JS, Hwang JW, Lee YS, Kang KS: Efficacy of sulforaphane is mediated by p38 MAP kinase and caspase-7 activations in ER-positive and COX-2-expressed human breast cancer cells. Eur J Cancer Prev. 2007 Dec;16(6):505-10. doi: 10.1097/01.cej.0000243856.97479.3b. [PubMed:18090122 ]
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